The optically active phenol derivative, more particularly, the phenol derivative (chemical name: (1R, 2S)-2-amino-1-(4-hydroxyphenyl)propan-1-ol) represented by the formula:
(wherein the carbon atoms marked with (R) and (S) have the same meanings as defined above) which is watched as an intermediate of medicaments and described to be useful in manufacturing, for example, 2-aminopropanol derivatives useful as agents for prevention or treatment of obesity, hyperglycemia or a disease caused by intestinal tract hypermotility (see the following literature 1), aminoethylphenoxyacetic acid derivatives useful as agents for pain remission and calculi removal promotion in urinary lithiasis (see the following literature 2), and phenoxyacetic acid derivatives useful as agents for prevention or treatment of pollakiuria, urinary incontinence, depression, biliary calculi or a diseases caused by hypermotility of biliary tract (see the following literature 3).
Thus far, as a production method of the optically active compound represented by the above formula (A), a method to obtain the compound represented by the above formula (A) by optical resolution with (−)-D-tartaric acid from a mixture of enantiomeric isomers represented by a formula:
(wherein the relative configuration of the amino group and the hydroxy group is erythro configuration) has been reported (see the following literature 4).
However, in the above method to produce the phenol derivative represented by the above formula (A), the mixture of the enanthiomeric isomers represented by the above formula (B) has to be optically resolved by using unnatural (−)-D-tataric acid unavailable easily, and in addition, the yield of the obtained phenol derivative represented by the above formula (A) is rather low of about 19%. Furthermore, it was an extremely wasteful method in that, for example, the most of the produced phenol derivative represented by the above formula (B) was wasted, because in the optical resolution of the mixture of enantiomeric isomers represented by the above formula (B), the other isomer of a desired isomer could not be recycled.
As mentioned above, the method that has been ever reported to produce the optically active phenol derivative represented by the above formula (A) has many problems, and is not a necessarily satisfactory production method in manufacture on an industrial scale and from the viewpoint of environmental aspects. Therefore, more effective and efficient method to produce the optically active phenol derivative represented by the above formula (A) has been desired.
Literature 1: JP Publication No. 2001-114736
Literature 2: WO99/05090 pamphlet
Literature 3: WO00/02846 pamphlet
Literature 4: Smith, Howard E., and other 4, Agonist effects of β-phenethylamines on the noradrenergic cyclic adenosine 3′,5′-monophosphate generating system in rat limbic forebrain., Journal of Medicinal Chemistry, 1977, Vol.20, No. 7, p. 978–981.